Composition and method



Patented May 26, 1942 Jo hull. Lontz, Wilmington, Del assig'norto E. I. du Pont de Nemours & Companyg'Wilmington,

I Del.,' a corporatio'n of Delaware No Drawing. Application March 11, 1941,

COMPOSITION AND METHOD 1 4 STIMULANT) I Serial NO. 382,72

v 12Claims.

This invention relates to plant stimulants and is particularly directed to plant stimulant compositions containingas an essential active'ingredient naphthylalkane sulfonic acid or. one :of its salts, particularlyan=alkali metalsalt, and to methods in which the-growthv characteristics of plants aremodifiedby application .ofsuch compounds.

In the scienceof phytology, or plant physiology, it is universally recognized that'certain factors regarded as growth regulatorsv or growthpromoting substances, both naturally occurring andsynthetic, are'responsible for the funda-' mental and directive development of plantlife. These plant growth substances, also known as auxins, plant hormones, plant growth stimulants, and referred to herein simply ask-plant stimulants}? in very minute: quantities promote and control the growth of -the plant cell, a property which can be determined qualitatively and quantitatively'by such .standard test procedures known as the Avena coleoptile curvature test of Boysen-Jensen (Growth Hormones in Plants. Translated and revised by G. :S. "Avery,

Jr., and P. R. Burkholder. McGraw-rHill, New York), the Avena cylinder or straight growth pp'. 463-518 (1938)). v v

While fundamentally these substances control the development-of the cell, particularly its elongation and division, the total orsuper'flcial responses to these substances are manifested in such various ways as'inducing nastic movement,

' bendirig andswelling, proliferation, and overgrowth ;of leaves and stems,'-control of, root growth, developmentof callous tissue, increased .cambial activity, and deposition of new cell wall and abscission tissue, and the initiation ofnew. roots on stems and leaves. The practical aspects of these properties. include propagation of plants from cuttings, hastening of ilower' bud "forma- I tion, hormonization of cereal'grains for con-- troling germination andgrowth, parthenogenic development of fruit, and delaying or controlling the fall of leaves, buds and fruit. v v

In the successful application of plant stimulants to various of these purposes it is important that the concentration of the compound in a suitable treating medium andthe time of treat? ment, both of which, particularly, with some Y. compounds, are highly critical, be adjustedcarefully. If this concentration/time Iactoris exceeded by using'either a higher concentration or longer treating time the stimulating efi'ect may 2 ,fectiveness. They have a favorable margin of vanish andinstead considerable to the plant develop.

Of the various type's' o'f known plant stimulants, an adequate summary of which may be. found in US. Patent 2,220,505, l-naphthaleneaceticlacid has probably obtained-the most significance in the art. On the basis of cost eificiency and 'ease of synthesis it appears to be most utstandin yet its synthesis' is by no means simple and its range of tolerance is too sharpto providesumcient margin Of safety'in the hands of unskilled workmen.

' I have now found that the naphthylalkanesulfonates have plant stimulating properties and maybe used in various typesjof compositions, and maybe. applied in difierent, manners to modify the growth characteristics or plants in numerous ways- The term .sulfonate'fis intended to apply, to boththe salts and the acids.

As compared with the prior art, compoundsof my invention are safe, effective and readily available. They may be prepared bysimpler and more efficient synthesis, and when applied inIproper concentrations have the same orderof efiectiveness and in some cases even greater-e1- safety and may be applied'in higher concentrations without deleteriously affecting the plants.

. The compounds of'm'y invention maybe prepared from l-haloalkylnaphthalenes and alkali suliites. .The preparation of sodium l-naphtliyl- ,methanesulfonate, for example, is described in Jo r..-chem; Society 1933 485.: Sodium beta- I naphthyIethanesuIfOnate is prepared in a similar manner by the reaction of 'beta-l-naphthylethylbromide and sodium sulfite, and sodium V gamma-l-naphthylpropanesulfonate is similarly prepared'by the reaction of gamma-l-naphthylpropylbromide and sodium. sulfit'e. Similar reactions may be carried out with other alkali 2 'sulfite and other naphthylalkyl halides, .and

other methods of preparation maybe used. 1 The sodiunisalt can be replaced by the free'acid '(the hydrogen" slilfonate) and other salts including potassium, calcium, iron, etc., as welljasthe salts derivedv from ammonia and organic bases,

.ffor example, 'trimethylamine, pyridine, and

v 1 cyclohexyla'mine;

Other typical compounds Qwhich'may be prepared in an analogousmanner an 1 llhthylmethane sulfonate)., beganinclude l-naphthylmethanesulfonic'acid (hydronaphthylethanesulfonic ac'id gamma-l-naphvthylprg:panesulfonic acid, potassium lnaphthylmethanesulfonate,- potassium beta lnaphthylethanesulfonate, potassium gamma-l-naphthyl- ,propanesul fonate, ammonium l-naphthylmethanesulfonate, ammoniumbeta-l-naphthyl- ,ethanesulfonate, ammonium gamma-l-naphthylpropanesulfonateg :2-naphthylmethanesulfonic; acid (hydrogen 2-naphthylmethane sulfonate.

oouomi, materials such as the soluble gums or resins maybe included; also; water-soluble polycharacterlstics, acccrdingto the type of plant terial from aqueous, solution," for example," .the efl e'ctivej 'concentrationis' considerably lowerthan taining'from 0.5 to 10 percent ome ingredient, ,depending' upon the type of plants used, or in atf 6 7 'nigs'. per liter after'3-hours' soaking with a A A-A .dustingtreatment to seeds concentrations "bel6 fonate), betaa-naphthylethanesulfonic A acid,y

sodium beta+2naphthylpropanesulfonate, calcium l-naphthylethanesulfonate; trimethylam- A moniumfl beta-i-naphthylethanesulfonate, and cyclohexylammonium l-naphthylmethanesub The compounds of this invention maybe used '1 in a variety of ways as stimuli to modify the; growth characteristics of plants; For examplelf they may be applied to seeds to" stimulate .root 10 and plumule development orto stimulate germination. They may be applied to cuttings, trans plantsor tubers to stimulate root formation, or, 1

they may be applied to intact plants tolpreventf premature drop ofAfr uitor foliage; They may induce parthenogeriesis. In their various applications they may be used on seedsor matureplants to regulate the development of the plants whenAAdesired to avoid drought, frost and other adversecondltions, Aorjto stimulate root activity in cut ings or transplanted plants for tomodify' the abscission cells to prevent premature drop of buds leaves, and jfruit. particularly apples. In all other applications they are; applied to liv ing'plant cells in such concentrations as will alter the growth characteristics'o f. the plant. In the application to'seeds' it is' notknownflwhether the actionis tomodifythe seed, per se or the plant which develops from theseje'd, and for the purposeof this invention it-will' be understood that 80 thet trm VpIant as used herein and in the appended claims is fintendedto include seeds A In the. application of the compound for these various'purposes different compositions may be employed. For the ,most part aqueous solutions will .be Afound'most desirable. j These solutions maylinclude' wetting agents oradhesives, or both.

iners such as polyvinyl alcohol, "The compounds '40 [also may, be "applied, in admixture :w ith-other 1 diluentselther as pastes or dustsli' Thus the ma;

,terials may be 'incorporated'in'oil's; fatsQor'simiIar A vehicles soon as lanolin, or in a finely divided inert such as talc, flour, fullers earth; clayjor othersoluble or insoluble; finely divided solids, v The effectiveness of the compounds of this invention will vary according to the individual Atreatmeritjandaccording to the vehicle from which the application is made. In applying ma-A 'endsfof thecuttings' may be'dipped in a dust con-,

an aqueous solution containing from 10-to 200 ,mgs'. p'erlliter', normally, 50-100 'mgs being suf- "gncient, depending upon the plant used and the time of treatment, Thus heavy rootin response A l p Also, goodlroot- A' ing response was obtained with carnation cuttings A -l-naphthylmethanesulfonate," sodium 6' beta-l-naphthylethanesulfonate and A 1 -gamma-l-naphthylpropanesulfonater' I T-In other applications dli'lTe'rent .-concentrations found most suitable, 'Thusin applyinga aaasoos A A A A tween 0.5 and 5 per cent are generally sufiicient,

and in aqueous solution the concentration may 10 to 200 grams per gallons of water, or in -the1cast ofa dustfromfl to 100 parts per 100,000,

can be used. It will readily be understood, how- .ever, that in somecases either higher or lower concentrations may be necessary.

While I have'disclosedmy invention withrefer ence to particularapplications it'is to be under-- stood that it is not'limited in these respects but is ;directed to the application of the particular stimulantdescribed in any manner whichleads to alteration of thegrowthcharacteristics of plants. A

The general characteristicofa plant stimulant is that of modifying the development of theplant, notsimply as=in the case of a fertilizer by providing a more proper. food A butA'Aactually, by altering the growth characteristics of the plant inthe variousways already-set forth, nor arethey to be confused with plant poisons" which simply alter and destroy. Additionally, the plant'stimulant is effective in minute amounts,.the effective concentrationAAbeing easily set forth in parts per million or--milligrams perliterr I i I Since many iwidely diflering embodiments of the invention maybe madeyitis to be understood that such modifications as come within the spirit or within the scope of the claims. A

I claim:

of the invention are. intended to be included 1 1. A plantstimulant.,composiition containing as an. essentialxactive insredient a" naphthylalkanesulfonate, AA I 2; A plant stimulant composition containing as I an [essential act iveinsredient- Aa ,l-naphthylal I kanesulfonate,

a. A plant stimulant oomposmon oonohm'ji. J an essential active ingredient an alkali l-naphthylalkanesulfonate,

4. In the propagationiofplantsthefmethodAof altering the, growth characteristics of themlant which comprises Atreatingtlie plant with a naph- A thylalkanesulfonate.

5,- In the propagation of plants the method of altering the growth characteristics of the plant which comprises treating the plant with" a 1-, i

naphthylalkanesulfonate.

' 6; In the propagation of plantslthe method of A altering the growth characteristics of the'plant which comprises treating; the plant with an alkali i-naphthylalkanesulfonate;

7. A plant stimulant composition containing: as an essential active ingredie'ntsodium Al-naphthylmethanesulfonate. A A

8. A plant stimulant composition containing as on essential active ingredient sodium beta-inaphthylethanesulfonate.

" 9. A plant stimulant composition as naphthylpropanesulfonaten an essential activeingredient sodium gamma-1- A on the propagation ofplants themethod of altering the growthcharacteris'tics of th'e'plant which comprises treating theplantwith sodium l-naphthylmethanesulfonate. 11. In the propagation ct'plants the'methodof;

altering the' growth characteristics of the plant which eompriseswtreating theplant with beta-"l-naphtliylethanesulfonate. A

' 12.1In' the propagation of plants the method of altering the growth characteristics of the'plant which-comprises: treatlngthe plant with againma-d naphthy b qp nesulfonate,A 1 

